Water → 4,6-Dimorpholino-5-fluoro-2-(4-phenylpiperazin-1-yl)pyrimidine

HRID 1044653Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1044653
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[C:11]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:10]=[C:9]([N:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:21][CH2:20]3)[N:8]=2)[CH2:3][CH2:2]1.[O-]S(C(F)(F)[F:36])(=O)=O.F[N+]1C(C)=CC(C)=CC=1C.O>ClCCl>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:12]([F:36])=[C:11]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:10]=[C:9]([N:19]3[CH2:20][CH2:21][N:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:23][CH2:24]3)[N:8]=2)[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 27245751-Fluoro-2,4,6-trimethylpyridinium Trifluoromethanesulfonate [Fluorinating Reagent]HCID 442504374,6-Dimorpholino-2-(4-phenylpiperazin-1-yl)pyrimidine

Produkt 1

HCID 442505004,6-Dimorpholino-5-fluoro-2-(4-phenylpiperazin-1-yl)pyrimidineAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The synthesis method shall be explained concretely, and in order, below. 4,6-dimorpholino-2-(4-phenylpiperazin-1-yl)pyrimidine (380 mg, 0.926 mmol) was dissolved in dichloromethane (5 ml), and N-fluoro-2,4,6-trimethylpyridinium triflate (402 mg, 1.39 mmol) was added. After agitation for 30 minutes at room temperature, water was added and extraction was done with dichloromethane. After washing the organic layer with saturated saline, drying was done with MgSO4, and the solvent was distilled away under reduced pressure. Purification was done by silica gel chromatography (hexane:ethyl acetate=4:1), and 122 mg of 4,6-dimorpholino-5-fluoro-2-(4-phenylpiperazin-1-yl)pyrimidine was obtained (yield 31%). The melting point measurement result, the MS measurement result, and the NMR data for the obtained Compound 82 are shown below.

Aufarbeitung

  1. customThe synthesis method
  2. extractionextraction
  3. washAfter washing the organic layer with saturated saline
  4. customdrying
  5. distillationthe solvent was distilled away under reduced pressure
  6. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-76a6e3b911c34f25b31dba654b45452f
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563715B2

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